Cell specific cytotoxicity and structure-activity relationship of lipophilic 1-B-D-arabinofuranosylcytosine (ara-C) derivatives

Nucleosides Nucleotides. 1999 Apr-May;18(4-5):877-8. doi: 10.1080/15257779908041589.

Abstract

Lipophilic derivatives of ara-C were developed with the aim to improve drug penetration and retention in solid tumors. Ara-C was esterified at the 5'-position with fatty acids (16-22 C-atoms, 0-3 double bonds). The derivatives were inactive in cell lines with various forms of ara-C and 2',2'-difluorodeoxycytidine (dFdC, gemcitabine) resistance, including deoxycytidine kinase (dCK) deficiency. The activity in the parent cell lines correlated negatively with chain length and positively with double bonds.

MeSH terms

  • Animals
  • Antimetabolites, Antineoplastic / chemistry
  • Antimetabolites, Antineoplastic / pharmacology*
  • Cytarabine / analogs & derivatives*
  • Cytarabine / chemistry
  • Cytarabine / pharmacology
  • Deoxycytidine / analogs & derivatives
  • Deoxycytidine / pharmacology
  • Drug Resistance, Neoplasm
  • Drug Screening Assays, Antitumor
  • Gemcitabine
  • Mice
  • Rats
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Antimetabolites, Antineoplastic
  • Cytarabine
  • Deoxycytidine
  • Gemcitabine